(2S)-1-[(benzyloxy)carbonyl]-4-phenyl-2,5-dihydro-1H-pyrrole-2-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】38574

【品名】(2S)-1-[(benzyloxy)carbonyl]-4-phenyl-2,5-dihydro-1H-pyrrole-2-carboxylic acid

【CA登记号】

【分子式】C₁₉H₁₇NO₄

【分子量】323.34832

【元素组成】C 70.58% H 5.3% N 4.33% O 19.79%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XXXI)

The Grignard condensation of N-(benzyloxycarbonyl)-4-oxo-L-proline (XXIX) with phenylmagnesium bromide gives the 4-hydroxy-4-phenylproline derivative (XXX), which is dehydrated with TFA yielding the dehydroproline (XXXI). The hydrogenation of (XXXI) with Li in liquid ammonia affords the previously reported trans-4-phenyl-L-proline (XIX), which is hydrogenated to the corresponding cyclohexyl derivative (XI) with H2 over PtO2.

参考文献中间体

合成目标

【1】 Powell, J.R.; Cushman, D.W.; Krapcho, J.; Turk, C.; DeForrest, J.M.; Spitzmiller, E.R.; Karanewsky, D.S.; Duggan, M.; Rovnyak, G.; Schwartz, J.; et al.; Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines. J Med Chem 1988, 31, 6, 1148.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XI)	38567	(2S,4S)-4-cyclohexyl-2-pyrrolidinecarboxylic acid	C₁₁H₁₉NO₂	详情	详情
(XIX)	38572	(2S,4S)-4-phenyl-2-pyrrolidinecarboxylic acid	C₁₁H₁₃NO₂	详情	详情
(XXIX)	11357	(2S)-1-[(Benzyloxy)carbonyl]-4-oxotetrahydro-1H-pyrrole-2-carboxylic acid	C₁₃H₁₃NO₅	详情	详情
(XXX)	38573	(2S,4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-4-phenyl-2-pyrrolidinecarboxylic acid	C₁₉H₁₉NO₅	详情	详情
(XXXI)	38574	(2S)-1-[(benzyloxy)carbonyl]-4-phenyl-2,5-dihydro-1H-pyrrole-2-carboxylic acid	C₁₉H₁₇NO₄	详情	详情

Extended Information